Ajmalicine

Base Information

• Chemical Name: Ajmalicine
• CAS No.: 483-04-5
• Molecular Formula: C21H24N2O3
• Molecular Weight: 352.433
• European Community (EC) Number: 207-589-5
• UNII: 4QJL8OX71Z
• DSSTox Substance ID: DTXSID60904151
• Nikkaji Number: J13.108C
• Wikipedia: Ajmalicine
• Wikidata: Q412957
• Pharos Ligand ID: 6YFW44CWRNZ4
• Metabolomics Workbench ID: 122970
• ChEMBL ID: CHEMBL123325
• Mol file: 483-04-5.mol

Synonyms:19-epiajmalicine;ajmalicine;ajmalicine hydrochloride;ajmalicine, (19alpha,20alpha)-isomer;ajmalicine, (19beta)-isomer;ajmalicine, (19beta,20alpha)-isomer;ajmalicine, (3-beta,19beta)-isomer;ajmalicine, (3beta,19alpha)-isomer;ajmalicine, (3beta,19alpha,20alpha)-isomer;ajmalicine, (hydrochloride(19beta,20alpha))-isomer;ajmalicine, hydrochloride(19alpha)-isomer;ajmalicine, PO4(19alpha)-isomer;akuammigine;delta-yohimbine;Lamuran;raubasine;raubasine HCl;raubasine hydrochloride;rauvasan;tetrahydro-alstonine;tetrahydroalstonine

Chemical Property of Ajmalicine

Chemical Property:

• Vapor Pressure: 4.47E-11mmHg at 25°C
• Melting Point: 258°C (rough estimate)
• Refractive Index: 1.656
• Boiling Point: 524.042 °C at 760 mmHg
• PKA: pK1:10.55(+1) (25°C)
• Flash Point: 270.731 °C
• PSA: 54.56000
• Density: 1.303 g/cm³
• LogP: 3.11670
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 352.17869263
• Heavy Atom Count: 26
• Complexity: 606

Purity/Quality:

99% ^*data from raw suppliers

Raubasine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 25-22
• Safety Statements: 22-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=CC=CC=C45
• Isomeric SMILES: C[C@H]1[C@H]2CN3CCC4=C([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC=CC=C45
• Description: Vinca rosea L. yields this alkaloid which crystallizes as colourless needles from MeOH. The base is laevorotatory having a specific rotation of [α]D_620 (MeOH) and forms a crystalline hydrochloride, m.p. 281-3°e. The structure given above has been elucidated from chemical and spectroscopic data.
• Uses: Antihypertensive, anti-ischemic. Antihypertensive, anti-ischemic (cerebral and peripheral)

Technology Process of Ajmalicine

There total 142 articles about Ajmalicine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

3-dehydroajmalicine perchlorate (85611-01-4) → ajmalicine (483-04-5)

Guidance literature:

With tri-n-butyl-tin hydride; In methanol; for 0.0833333h; Ambient temperature;

DOI:10.1055/s-1985-31434

Reference yield: 45.0%

2,3-secoajmalicine (68780-83-6) → ajmalicine (483-04-5)

Guidance literature:

2,3-secoajmalicine; With mercury(II) diacetate; edetate disodium; acetic acid; In water; at 80 - 100 ℃; for 8h; Inert atmosphere;

With sodium tetrahydroborate; sodium hydroxide; In methanol; water; at 0 ℃; for 0.333333h; pH=Ca. 9 - 10; Inert atmosphere;

Reference yield:

serpentine (47485-82-5) → ajmalicine (483-04-5)

Guidance literature:

With potassium hydroxide; platinum; Hydrogenation;

DOI:10.1002/hlca.19520350525 DOI:10.1021/ja01540a027

upstream raw materials:

serpentine

tryptamine

(4S)-5c-formyl-4r-methoxycarbonylmethyl-6t-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

(4aS)-7-(2-indol-3-yl-ethyl)-1c-methyl-6-oxo-(4ar,8at)-4a,5,6,7,8,8a-hexahydro-1H-pyrano[3,4-c]pyridine-4-carboxylic acid methyl ester

Downstream raw materials:

tetrahydroalstonine

ajmalicine 17-methyl acetal

ajmalicine hemiacetal

(7aR,8S,10R,11aR,12aS)-8-Methyl-5,6,7a,8,10,11,11a,12,12a,13-decahydro-7H-9-oxa-6a,13-diaza-indeno[2,1-a]anthracen-10-ol

Refernces

• 1、 MacKellar,F.A. et al.. "-". . p. 7155 - 7156. Retrieved 1973.
• 2、 Brown et al.. "-". . p. 636. Retrieved 1977.
• 3、 -. "ENANTIOSELECTIVE SYNTHESES OF HETEROYOHIMBINE NATURAL PRODUCT INTERMEDIATES". Paragraph 00072; 00073. . Retrieved 2016/11/21.
• 4、 Brown, Richard T.,Dauda, Bukar E.N.,Pratt, Simon B.,Richards, Paul. "Short stereoselective syntheses of (-)-ajmalicine, (-)-3-iso-ajmalicine and their 5-methoxycarbonyl derivatives from secologanin". . p. 51 - 58. Retrieved 2007/10/03.